Vat dyestuffs oe the indigoid series



Patented May 27, 1930 UNITED STATES 1,760,769 PATENT? OFFICE} WILEEEMEEELM IEE, or LEVERKUSEN,

NEAR; ooLoGNE-oN-rHE-Enmia, AND rHEo:

Don NOCKEN, or WIESDORF, NEAR coEoeNE-oN-TnE-RHmE, eEEMANY,..AssIGN-' ons TO GENERAL ANILiNE worms, me, on NEW YORK, N, Y., A CORPORATION OF DELAWARE V AT DYESTUFFS OF THE INDIGOID SERIES No Drawing. Application filed March 25, 1927, Serial No." 1'8,495, and in Germany April 3, 1926.

The present invention relates to the production of new vat dyestufiis, resulting from the Condensation of a thio ether of a l-hydroxyt-mercapto compound of the following formula A Y OH in which X represents an alkyl, aralkyl or aryl group and Y represents hydrogen which may be substituted by an halogen or an alkyl group, with such an isatin body of the general formula organic solvents they crystallize mostly in the form of needles possessing a metallic.

luster. They are soluble in pyridine with a blue to green coloration and yield with alkaline hydrosulfite yellow to orange vats,

from which they dye vegetable fibres blue to A green shades. Our new dyestufis are distinguished from dyestuffs derived from alkyl or aryl ethers of 1.4-dihydroxy-naphthalene by their more greenish-blue to green shades and better fastness to light. The general formula of our dyestuifs is and R represents an aryl'residue which may bright shades I contain further substituents, preferably halogenatoms.

To further illustrate our invention the following example is given 1 Ewaxm-ple 1.190 parts 'monomethyl thio ether of 4-mercapto-1-hydroxynaphthalene (Ber. 48, page 128) are dis solved in 2000 parts by weight of benzene and condensed with the di-bromo-isatinchloride prepared in the customary manner, from 305 parts by weight of 5.7-dibronmisatin and 230 parts by weight of phosphorous pentaby weight of the chloride in chlorbenzene solution. After a short time the dyestufi' crystallizes out. It is soluble with difficulty in sulfuric acid, more readily soluble in pyridine with a bluishgreen coloration and dyes the fiber from the yellow alkaline hydrosulfite vat in clear and fast greenish-blue shades. Our dyestutf has probably the following formula naphthol (prepared from alphanaphthol and p-tolyl-sulfur chloride according to Zincke and Farr, annalen 391, page 63) is condensed with the equivalent amount of 5.7 -dibromisatinchloride, in the manner described in Example 1. The dyestutf crystallizes from chlorbenzene in the form of needles possessing a bronze luster. The new dyestufl dyes cotton from the alkaline hydrosulfite vat in very greenish-blue shades. It has most probably the following formula 2.-'266 parts by weight of the I Another very good dyestufi' is obtained from 4-ethyl-mercapto-1-naphthol by condensation with 1-chlor-brom-2.3-naphthisatin, which has probably the following formula o E t 9 (I is I ZZH; E

The naphthisatin may be obtained by brominating according to the" usual method 1-chloro-2, 3-naphthisatin; It is a red crystalline powder melting at about 313 C; (compare D. R. P. 273,536, Friedl. XI, 309).

The orientation of the bromine atom is not definitely known. This dyestufi' yields a yleil'y bright greenish shade especially fast to We claim v A 1. As new compounds vat dyestuffs, having most probably the general formula in which represents an a1 1, aralkyl or aryl grou Y represents hy rogen which may be en stituted by an'halogen-or by an alkyl group, and R represents an aryl residue which may contain further substituents which dyestuffs are, when dry, powders having a metallic luster yielding with alkaline hydrosulfite a yellow to orange vat from which fibres are dyed in blue-green to greenish shades of excellent fastness especially to light, and which are substantially identical with the dyestuifs obtainable by condensing with an isatin body a thioether of a 4-mercapto-l-naphthol com ound corresponding most probably to the ormula V Y on wherein X re' resents an alkyl, aralkyl or aryl group, an Y represents hydrogen whlch may be substituted by an halogen or by an alkyl group.

' halogen or alkyl group,

A 2. As new compounds vat dyestufls cor're: spending probably to the following formula be substituted by an which dyestuffs are, when dried, powders having a metallic luster, yielding with alkaline hydrosulfite a yellow to orange'vat from which fibres are dyed full bluish-green to green shades of excellent fastan hydrogen which may ness especially to light, said dyestuffs being substantially identical with the dyestufis obtainable by condensing an isatin chloride with an alkyl thio ether of a 4-mercapto-1- hydroxy-naphthalene compound having the' general formula in which X represents an alkyl and Y repre-' sents hydrogen which may be substituted by an halogen or an alkyl group.

3. A new vat dyestufi corresponding probably to the following formula THEODOR N OCKEN WILHELM NEELMEIER:

' I in which X represents alkyl and Y represents- 

